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Theoretical and Experimental Spectroscopic Analysis of Cyano-Substituted Styrylpyridine Compounds

A combined theoretical and experimental study on the structure, infrared, UV-Vis and (1)H NMR data of trans-2-(m-cyanostyryl)pyridine, trans-2-[3-methyl-(m-cyanostyryl)] pyridine and trans-4-(m-cyanostyryl)pyridine is presented. The synthesis was carried out with an efficient Knoevenagel condensatio...

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Autores principales: Castro, Maria Eugenia, Percino, Maria Judith, Chapela, Victor M., Ceron, Margarita, Soriano-Moro, Guillermo, Lopez-Cruz, Jorge, Melendez, Francisco J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588082/
https://www.ncbi.nlm.nih.gov/pubmed/23429190
http://dx.doi.org/10.3390/ijms14024005
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author Castro, Maria Eugenia
Percino, Maria Judith
Chapela, Victor M.
Ceron, Margarita
Soriano-Moro, Guillermo
Lopez-Cruz, Jorge
Melendez, Francisco J.
author_facet Castro, Maria Eugenia
Percino, Maria Judith
Chapela, Victor M.
Ceron, Margarita
Soriano-Moro, Guillermo
Lopez-Cruz, Jorge
Melendez, Francisco J.
author_sort Castro, Maria Eugenia
collection PubMed
description A combined theoretical and experimental study on the structure, infrared, UV-Vis and (1)H NMR data of trans-2-(m-cyanostyryl)pyridine, trans-2-[3-methyl-(m-cyanostyryl)] pyridine and trans-4-(m-cyanostyryl)pyridine is presented. The synthesis was carried out with an efficient Knoevenagel condensation using green chemistry conditions. Theoretical geometry optimizations and their IR spectra were carried out using the Density Functional Theory (DFT) in both gas and solution phases. For theoretical UV-Vis and (1)H NMR spectra, the Time-Dependent DFT (TD-DFT) and the Gauge-Including Atomic Orbital (GIAO) methods were used, respectively. The theoretical characterization matched the experimental measurements, showing a good correlation. The effect of cyano- and methyl-substituents, as well as of the N-atom position in the pyridine ring on the UV-Vis, IR and NMR spectra, was evaluated. The UV-Vis results showed no significant effect due to electron-withdrawing cyano- and electron-donating methyl-substituents. The N-atom position, however, caused a slight change in the maximum absorption wavelengths. The IR normal modes were assigned for the cyano- and methyl-groups. (1)H NMR spectra showed the typical doublet signals due to protons in the trans position of a double bond. The theoretical characterization was visibly useful to assign accurately the signals in IR and (1)H NMR spectra, as well as to identify the most probable conformation that could be present in the formation of the styrylpyridine-like compounds.
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spelling pubmed-35880822013-03-13 Theoretical and Experimental Spectroscopic Analysis of Cyano-Substituted Styrylpyridine Compounds Castro, Maria Eugenia Percino, Maria Judith Chapela, Victor M. Ceron, Margarita Soriano-Moro, Guillermo Lopez-Cruz, Jorge Melendez, Francisco J. Int J Mol Sci Article A combined theoretical and experimental study on the structure, infrared, UV-Vis and (1)H NMR data of trans-2-(m-cyanostyryl)pyridine, trans-2-[3-methyl-(m-cyanostyryl)] pyridine and trans-4-(m-cyanostyryl)pyridine is presented. The synthesis was carried out with an efficient Knoevenagel condensation using green chemistry conditions. Theoretical geometry optimizations and their IR spectra were carried out using the Density Functional Theory (DFT) in both gas and solution phases. For theoretical UV-Vis and (1)H NMR spectra, the Time-Dependent DFT (TD-DFT) and the Gauge-Including Atomic Orbital (GIAO) methods were used, respectively. The theoretical characterization matched the experimental measurements, showing a good correlation. The effect of cyano- and methyl-substituents, as well as of the N-atom position in the pyridine ring on the UV-Vis, IR and NMR spectra, was evaluated. The UV-Vis results showed no significant effect due to electron-withdrawing cyano- and electron-donating methyl-substituents. The N-atom position, however, caused a slight change in the maximum absorption wavelengths. The IR normal modes were assigned for the cyano- and methyl-groups. (1)H NMR spectra showed the typical doublet signals due to protons in the trans position of a double bond. The theoretical characterization was visibly useful to assign accurately the signals in IR and (1)H NMR spectra, as well as to identify the most probable conformation that could be present in the formation of the styrylpyridine-like compounds. MDPI 2013-02-18 /pmc/articles/PMC3588082/ /pubmed/23429190 http://dx.doi.org/10.3390/ijms14024005 Text en © 2013 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0 This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Castro, Maria Eugenia
Percino, Maria Judith
Chapela, Victor M.
Ceron, Margarita
Soriano-Moro, Guillermo
Lopez-Cruz, Jorge
Melendez, Francisco J.
Theoretical and Experimental Spectroscopic Analysis of Cyano-Substituted Styrylpyridine Compounds
title Theoretical and Experimental Spectroscopic Analysis of Cyano-Substituted Styrylpyridine Compounds
title_full Theoretical and Experimental Spectroscopic Analysis of Cyano-Substituted Styrylpyridine Compounds
title_fullStr Theoretical and Experimental Spectroscopic Analysis of Cyano-Substituted Styrylpyridine Compounds
title_full_unstemmed Theoretical and Experimental Spectroscopic Analysis of Cyano-Substituted Styrylpyridine Compounds
title_short Theoretical and Experimental Spectroscopic Analysis of Cyano-Substituted Styrylpyridine Compounds
title_sort theoretical and experimental spectroscopic analysis of cyano-substituted styrylpyridine compounds
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588082/
https://www.ncbi.nlm.nih.gov/pubmed/23429190
http://dx.doi.org/10.3390/ijms14024005
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